*Note: I use a combination of Wilton's Light Cocoa and Dark Cocoa Candy Melts. If you use chocolate chips, you will need to either temper the chocolate, or try to keep the treats refrigerated. You can also use any other color of Candy Melts to match with your school's colors.
Begin by melting the chocolate. I use the microwave on 30% power for about 2-3 minutes, then stir... then again in 30-second intervals at 30% power until the chocolate is smooth.

Brush the chocolate, using a food-safe paintbrush, up the sides of a cupcake liner. Fill the pan, and allow to rest in the refrigerator for about 5-10 minutes to firm up completely.

Prepare your filling.
I used my Homemade Peanut Butter Cup Filling and Chocolate Ganache Filling (which I made as described in the icing recipe, but then placed in the refrigerator for an hour or so to get it nice and set).
I also crushed up a graham cracker to add with some marshmallow cream - these ended up a little too messy. If I did it again, I may mix the graham cracker crumbs with a little melted butter to make it more of a crust in there that would stick together better. (Let me know if you try it that way and like it!)

When the chocolate cups are set, fill each cup with about 1-2 tsp. of filling. My trusty scoop that I use for everything (cake pops, especially) was the perfect size.

You then will want to press the filling down to flatten it. Be careful here that you don't press too hard when flattening or you can crack the chocolate cup.

Cover the top of the filling with melted chocolate, and again use the paintbrush to help spread it to look nice and smooth.

Insert your lollipop stick immediately into the candy. Because your fillings are likely cool from the refrigerator, you need to be sure to put that stick in immediately or the chocolate will set, and you can't get a stick in there.

Once you get all of them covered and stick-ed (stuck??)... put them in the refrigerator again for about 10-15 minutes to be sure the sticks stay in well.

To make the 'mortarboard' or top part of the hat, spread the candy on waxed or parchment paper, and cut into about 2" squares.

To assemble the caps, peel the paper off of the candy cup. Brush a little melted chocolate on top to act as glue. Place a chocolate square on top. Add a tassel (made by rolling a Tootsie Roll into a thin rope and smashing one end flat). And top it off with an M&M.